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Literature DB >> 12240364

Palladium-catalysed intramolecular annulation of 2-haloanilines and ketones: enolate arylation vs. nucleophilic addition to the carbonyl group.

D Solé¹, L Vallverdú, E Peidró, J Bonjoch.

Abstract

Two alternative annulation pathways involving either the enolate arylation or the addition to the ketone carbonyl group can operate in the Pd-catalysed intramolecular coupling of 2-haloanilines and ketones.

Entities: Chemical

Year: 2001 PMID： 12240364 DOI： 10.1039/b105686g

Source DB: PubMed Journal: Chem Commun (Camb) ISSN： 1359-7345 Impact factor: 6.222

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Cited

3 in total

1. Concise Total Synthesis of (-)-Affinisine Oxindole, (+)-Isoalstonisine, (+)-Alstofoline, (-)-Macrogentine, (+)-N_a -Demethylalstonisine, (-)-Alstonoxine A, and (+)-Alstonisine.

Authors: Michael Rajesh Stephen; M Toufiqur Rahman; V V N Phani Babu Tiruveedhula; German O Fonseca; Jeffrey R Deschamps; James M Cook
Journal: Chemistry Date: 2017-10-18 Impact factor: 5.236

2. Palladium-catalyzed α-arylation of carbonyls in the de novo synthesis of aromatic heterocycles.

Authors: Harish K Potukuchi; Anatol P Spork; Timothy J Donohoe
Journal: Org Biomol Chem Date: 2015-04-21 Impact factor: 3.876

3. Stereoselective synthesis of tricyclic compounds by intramolecular palladium-catalyzed addition of aryl iodides to carbonyl groups.

Authors: Jakub Saadi; Christoph Bentz; Kai Redies; Dieter Lentz; Reinhold Zimmer; Hans-Ulrich Reissig
Journal: Beilstein J Org Chem Date: 2016-06-16 Impact factor: 2.883

3 in total

Palladium-catalysed intramolecular annulation of 2-haloanilines and ketones: enolate arylation vs. nucleophilic addition to the carbonyl group.

1. Concise Total Synthesis of (-)-Affinisine Oxindole, (+)-Isoalstonisine, (+)-Alstofoline, (-)-Macrogentine, (+)-Na -Demethylalstonisine, (-)-Alstonoxine A, and (+)-Alstonisine.

2. Palladium-catalyzed α-arylation of carbonyls in the de novo synthesis of aromatic heterocycles.

3. Stereoselective synthesis of tricyclic compounds by intramolecular palladium-catalyzed addition of aryl iodides to carbonyl groups.

1. Concise Total Synthesis of (-)-Affinisine Oxindole, (+)-Isoalstonisine, (+)-Alstofoline, (-)-Macrogentine, (+)-N_a -Demethylalstonisine, (-)-Alstonoxine A, and (+)-Alstonisine.